When I got this bike (the '11 SERGU) I did it a little differently than prior bikes. I did the "break in" the first 50 miles, then dumped the Syn 3, changed the filter, and put Mobil 1 in the crankcase. I spent about 2 hours putting that first 50 miles on, and dumped the Syn 3 just because I don't like it. At 1K, I changed to Redline products in all holes...20W50, Shockproof, and MTL. Also a K&N oil filter...mostly because they are easier to change with the nut welded to the end of the filter. The 1K service was probably unecessary in the crankcase, but I did it anyway, just to have the records that HD wants for warranty purposes.
I broke this engine in differently than my prior 103". I did not follow the HD owner's manual guidelines per se, but did it based on some other information I gathered concerning seating the rings properly. I've not used a drop of oil in the first 5K (actually 4K).
As Jerry mentioned, most of the oil change intervals and "advice" is based on things we had to do back in the bad old days of poorer oil products, less efficient combustion, and not so good oil filters. I never change oil more often than every 5K on any vehicle nowadays, and haven't for many years, since I stopped owning/driving cars/trucks built in the 60's and 70's, which wasn't all that long ago for me. The truth is that with synthetics, the intervals could be much, much longer than even the recommended intervals.